Stephen Chamberland

Assistant Professor, Organic Chemistry

Phone: (509) 963-1126
Fax: (509) 963-1050
Email: chambers@cwu.edu

Education:

• 2005 - Ph.D. Chemistry, University of California, Irvine; Advisor: Professor Keith A. Woerpel
• 1999 - B.S. Biochemistry, Boston College

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Professional Experience:

• March 2008 - Present, Assistant Professor, Department of Chemistry, Central Washington University
• Sept. 2005 - Feb. 2008, Postdoctoral Research Associate, Department of Chemistry, Colorado State University; Advisor: Professor Robert M. Williams

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Research Interests:

My research interests begin with pioneering new chemical methods and improving extant synthetic methods to make them useful. The application of many reported synthetic methods is hampered by a lack of substrate generality, poor yield in all but a few select examples, and metal-mediated reactions that are catalytic and asymmetric with respect to the metal/ligand complex, but are wasteful in other aspects. Along with the development of new and improved methods, I will undertake the total synthesis of structurally intreguing and biologically active natural products. I am also driven to broaden the use of computational chemistry in the synthetic arena by using it as a predictive tool used to plan natural product syntheses and also to rationalize the sometimes surprising stereochemical and regiochemical outcomes that befall synthetic chemists, often necessitating a change in strategy. Projects in my group will initially involve the design of new, better, and more environmentally friendly catalytic, asymmetric reactions to form nitrogen-containing three-membered rings, as well as pioneering new chemistry involving HOMO(Highest Occupied Molecular Orbital)-raising chiral auxiliaries in reactions such as the Diels-Alder [4 + 2] cycloaddition.

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Publications:

• Chamberland, S.; Sherman, D. H.; Williams, R. M. "Synthesis of Potential Early-Stage Intermediates in the Biosynthesis of FR900482 and Mitomycin C." Submitted for publication.
• Namiki, H. N.; Chamberland, S.; Gubler, D. A.; Williams, R. M. "Synthetic and Biosynthetic Studies of FR900482 and Mitomycin C: An Efficient and Stereoselective Hydroxymethylation of an Advanced Benzazocane Intermediate." Org. Lett. 2007, 9, 5341-5344.
• Chamberland, S.; Ziller, J. W.; Woerpel, K. A. "Structural Evidence that Alkoxy Substituents Adopt Electronically Preferred Pseudoaxial Orientations in Six-Membered Ring Dioxocarbenium Ions." J. Am. Chem. Soc. 2005, 127, 5322-5323.
• Chamberland, S.; Woerpel, K. A. "Using Nucleophilic Substitution Reactions to Understand How a Remote Alkyl or Alkoxy Substituent Influences the Conformation of Eight-Membered Ring Oxocarbenium Ions." Org. Lett. 2004, 6, 4739-4741.
• Kelly, T. R.; Chamberland, S.; Silva, R. A. "The Total Synthesis of Luotonin A." Tetrahedron Lett. 1999, 40, 2723-2724.

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